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Updated: Sep 13, 2025
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Smiles-Truce Cascades Enable Heteroaryl Cyclopropane and Sultine Synthesis
Thomas Sephton1, Zi Liu1, Michael F Greaney1
1School of Chemistry, University of Manchester, Manchester, M13 9PL, UK.
Abstract:
We describe a triple C─C bond cascade process for heteroaryl cyclopropane synthesis, through the reaction of vinyl sulfonium salts and sulfones under mild conditions. An initial conjugate addition (C─C bond 1) sets up a Smiles-Truce rearrangement (C─C bond 2), with a final 3-exo-tet ring closure (C─C bond 3) affording cyclopropanes. Serendipitously, we uncovered a novel reaction variant that affords sultines, an under-explored heterocycle with potential application as a bioisostere in medicinal chemistry.
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